Cinnarizinium fumarate.

In the title salt {systematic name: 4-diphenyl-methyl-1-[(E)-3-phenyl-prop-2-en-1-yl]piperazin-1-ium (2Z)-3-carb-oxy-prop-2-enoate}, C26H29N2(+)·C4H3O4(-), the piperazine ring in the cation adopts a distorted chair conformation and contains a positively charged N atom with quaternary character. The dihedral angle between the mean planes of the phenyl rings of the diphenyl-methyl group is 74.2 (7)° and those between these rings and the phenyl ring of the 3-phenyl-prop-2-en-1-yl group are 12.7 (9) and 80.6 (8)°. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds form chains along [001]. Weak C-H⋯O inter-actions connect parallel chains along [010], forming layers perpendicular to the a-axis direction.

Related literature

For cinnarizine as a calcium channel blocker, see: Terland & Flatmark (1999 ▶), as a nootropic drug, see: Towse (1980 ▶) and for a clinical evaluation in various allergic disorders, see: Barrett & Zolov (1960 ▶). For related structures, see: Bertolasi et al. (1980 ▶); Dayananda et al. (2012 ▶); Jasinski et al. (2011 ▶); Mouillé et al. (1975 ▶); Siddegowda et al. (2011 ▶); Song et al. (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C26H29N2 +·C4H3O4 −

M = 484.58

Monoclinic,

a = 21.9467 (4) Å

b = 10.43729 (18) Å

c = 11.20623 (19) Å

β = 90.0458 (15)°

V = 2566.95 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.67 mm−1

T = 123 K

0.60 × 0.30 × 0.25 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis RED and CrysAlis PRO; Agilent, 2011 ▶) T min = 0.732, T max = 1.000

9777 measured reflections

5146 independent reflections

4289 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.121

S = 1.02

5146 reflections

333 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812051239/zl2527sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051239/zl2527Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051239/zl2527Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H29N2+·C4H3O4−	F(000) = 1032
Mr = 484.58	Dx = 1.254 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3517 reflections
a = 21.9467 (4) Å	θ = 3.9–75.4°
b = 10.43729 (18) Å	µ = 0.67 mm−1
c = 11.20623 (19) Å	T = 123 K
β = 90.0458 (15)°	Prism, colorless
V = 2566.95 (8) Å3	0.60 × 0.30 × 0.25 mm
Z = 4

Agilent Xcalibur (Ruby, Gemini) diffractometer	5146 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4289 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.5081 pixels mm-1	θmax = 75.6°, θmin = 4.0°
ω scans	h = −23→27
Absorption correction: multi-scan (CrysAlis RED and CrysAlis PRO; Agilent, 2011)	k = −12→8
Tmin = 0.732, Tmax = 1.000	l = −13→13
9777 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0628P)2 + 0.4518P] where P = (Fo2 + 2Fc2)/3
5146 reflections	(Δ/σ)max = 0.001
333 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.70117 (5)	0.78316 (11)	0.33222 (10)	0.0323 (3)
O2	0.76739 (6)	0.88857 (12)	0.44702 (12)	0.0446 (3)
O3	0.64077 (5)	0.41055 (10)	0.57965 (9)	0.0298 (2)
O4	0.70688 (5)	0.50977 (10)	0.69945 (9)	0.0272 (2)
N1	0.79869 (5)	0.16984 (11)	0.86255 (10)	0.0208 (2)
N2	0.68573 (5)	0.31174 (11)	0.84519 (10)	0.0200 (2)
C1	0.87241 (6)	0.02312 (14)	0.76576 (13)	0.0237 (3)
C2	0.85173 (7)	−0.09616 (15)	0.80480 (14)	0.0287 (3)
H2A	0.8321	−0.1028	0.8780	0.034*
C3	0.86015 (7)	−0.20467 (16)	0.73566 (16)	0.0340 (3)
H3A	0.8461	−0.2837	0.7625	0.041*
C4	0.88951 (7)	−0.19554 (17)	0.62621 (16)	0.0362 (4)
H4A	0.8954	−0.2685	0.5800	0.043*
C5	0.90995 (7)	−0.07792 (18)	0.58618 (15)	0.0367 (4)
H5A	0.9293	−0.0716	0.5126	0.044*
C6	0.90159 (7)	0.03164 (16)	0.65610 (13)	0.0288 (3)
H6A	0.9156	0.1105	0.6291	0.035*
C7	0.86398 (6)	0.14289 (13)	0.84173 (12)	0.0223 (3)
H7A	0.8818	0.2158	0.7990	0.027*
C8	0.89718 (6)	0.12793 (13)	0.96069 (13)	0.0241 (3)
C9	0.95738 (7)	0.16951 (15)	0.96988 (15)	0.0315 (3)
H9A	0.9759	0.2094	0.9052	0.038*
C10	0.98986 (8)	0.15168 (18)	1.07497 (17)	0.0396 (4)
H10A	1.0300	0.1796	1.0803	0.048*
C11	0.96277 (8)	0.09271 (17)	1.17150 (16)	0.0402 (4)
H11A	0.9847	0.0802	1.2416	0.048*
C12	0.90255 (8)	0.05206 (15)	1.16380 (14)	0.0348 (4)
H12A	0.8842	0.0127	1.2290	0.042*
C13	0.86965 (7)	0.07003 (14)	1.05883 (14)	0.0280 (3)
H13A	0.8293	0.0434	1.0542	0.034*
C14	0.79157 (6)	0.29648 (13)	0.91797 (12)	0.0215 (3)
H14A	0.8042	0.3624	0.8622	0.026*
H14B	0.8174	0.3022	0.9881	0.026*
C15	0.72582 (6)	0.31822 (13)	0.95322 (11)	0.0205 (3)
H15A	0.7134	0.2535	1.0103	0.025*
H15B	0.7217	0.4015	0.9908	0.025*
C16	0.69605 (6)	0.18874 (13)	0.78029 (12)	0.0220 (3)
H16A	0.6727	0.1888	0.7068	0.026*
H16B	0.6820	0.1179	0.8290	0.026*
C17	0.76314 (6)	0.17046 (14)	0.75159 (12)	0.0226 (3)
H17A	0.7689	0.0901	0.7096	0.027*
H17B	0.7771	0.2394	0.7003	0.027*
C18	0.61896 (6)	0.32482 (14)	0.87638 (12)	0.0241 (3)
H18A	0.5951	0.3275	0.8035	0.029*
H18B	0.6062	0.2504	0.9217	0.029*
C19	0.60671 (6)	0.44322 (14)	0.94778 (13)	0.0243 (3)
H19A	0.6144	0.5229	0.9137	0.029*
C20	0.58525 (6)	0.43782 (14)	1.05838 (13)	0.0234 (3)
H20A	0.5786	0.3563	1.0892	0.028*
C21	0.57077 (6)	0.54589 (14)	1.13783 (12)	0.0235 (3)
C22	0.57635 (6)	0.67372 (15)	1.10234 (13)	0.0265 (3)
H22A	0.5904	0.6926	1.0261	0.032*
C23	0.56116 (7)	0.77284 (15)	1.17925 (14)	0.0307 (3)
H23A	0.5651	0.8574	1.1543	0.037*
C24	0.54012 (7)	0.74589 (16)	1.29343 (14)	0.0305 (3)
H24A	0.5295	0.8123	1.3447	0.037*
C25	0.53502 (7)	0.61982 (17)	1.33073 (13)	0.0318 (3)
H25A	0.5213	0.6015	1.4073	0.038*
C26	0.55045 (7)	0.52071 (15)	1.25361 (13)	0.0282 (3)
H26A	0.5472	0.4363	1.2795	0.034*
C100	0.73414 (7)	0.79844 (14)	0.43019 (13)	0.0269 (3)
C101	0.72630 (7)	0.69456 (14)	0.51966 (13)	0.0253 (3)
H10B	0.7510	0.6958	0.5871	0.030*
C102	0.68628 (7)	0.60047 (13)	0.50916 (12)	0.0233 (3)
H10C	0.6627	0.5971	0.4402	0.028*
C103	0.67661 (6)	0.49876 (13)	0.60193 (12)	0.0222 (3)
H1N	0.6971 (8)	0.3776 (18)	0.7921 (17)	0.027 (4)*
H1O1	0.7076 (11)	0.851 (2)	0.279 (2)	0.054 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0442 (6)	0.0275 (5)	0.0254 (5)	−0.0047 (5)	−0.0059 (4)	0.0074 (4)
O2	0.0537 (8)	0.0318 (6)	0.0484 (7)	−0.0153 (6)	−0.0188 (6)	0.0135 (5)
O3	0.0385 (6)	0.0226 (5)	0.0282 (5)	−0.0041 (4)	−0.0018 (4)	−0.0003 (4)
O4	0.0407 (6)	0.0207 (5)	0.0201 (5)	−0.0006 (4)	−0.0027 (4)	0.0004 (4)
N1	0.0217 (5)	0.0202 (5)	0.0204 (5)	0.0032 (4)	−0.0016 (4)	−0.0015 (4)
N2	0.0219 (5)	0.0201 (5)	0.0180 (5)	0.0036 (4)	−0.0001 (4)	0.0003 (4)
C1	0.0185 (6)	0.0249 (7)	0.0278 (7)	0.0044 (5)	−0.0032 (5)	−0.0019 (5)
C2	0.0270 (7)	0.0267 (7)	0.0325 (8)	0.0022 (6)	0.0005 (5)	−0.0027 (6)
C3	0.0296 (8)	0.0264 (8)	0.0461 (9)	0.0017 (6)	−0.0042 (6)	−0.0054 (7)
C4	0.0295 (8)	0.0349 (8)	0.0443 (9)	0.0068 (7)	−0.0036 (6)	−0.0173 (7)
C5	0.0304 (8)	0.0484 (10)	0.0313 (8)	0.0058 (7)	0.0020 (6)	−0.0109 (7)
C6	0.0260 (7)	0.0322 (8)	0.0282 (7)	0.0035 (6)	−0.0005 (5)	−0.0012 (6)
C7	0.0219 (6)	0.0212 (6)	0.0239 (6)	0.0008 (5)	−0.0003 (5)	0.0009 (5)
C8	0.0247 (7)	0.0198 (6)	0.0280 (7)	0.0055 (5)	−0.0029 (5)	−0.0042 (5)
C9	0.0253 (7)	0.0306 (8)	0.0387 (8)	0.0035 (6)	−0.0022 (6)	−0.0071 (6)
C10	0.0272 (8)	0.0444 (10)	0.0473 (10)	0.0080 (7)	−0.0112 (7)	−0.0136 (8)
C11	0.0448 (9)	0.0386 (9)	0.0372 (9)	0.0195 (8)	−0.0199 (7)	−0.0115 (7)
C12	0.0511 (10)	0.0252 (7)	0.0282 (7)	0.0105 (7)	−0.0045 (7)	−0.0010 (6)
C13	0.0320 (7)	0.0218 (7)	0.0303 (7)	0.0024 (6)	−0.0037 (6)	−0.0006 (6)
C14	0.0234 (6)	0.0208 (6)	0.0202 (6)	0.0014 (5)	−0.0012 (5)	−0.0009 (5)
C15	0.0235 (6)	0.0216 (6)	0.0163 (6)	0.0026 (5)	−0.0015 (4)	−0.0003 (5)
C16	0.0241 (7)	0.0223 (6)	0.0197 (6)	0.0016 (5)	−0.0025 (5)	−0.0015 (5)
C17	0.0246 (7)	0.0238 (7)	0.0193 (6)	0.0043 (5)	−0.0015 (5)	−0.0023 (5)
C18	0.0205 (6)	0.0282 (7)	0.0237 (6)	0.0026 (5)	−0.0009 (5)	0.0009 (5)
C19	0.0215 (6)	0.0256 (7)	0.0260 (7)	0.0043 (5)	0.0001 (5)	0.0028 (6)
C20	0.0192 (6)	0.0246 (7)	0.0265 (7)	0.0012 (5)	−0.0012 (5)	0.0011 (5)
C21	0.0177 (6)	0.0283 (7)	0.0246 (7)	0.0001 (5)	−0.0004 (5)	−0.0003 (5)
C22	0.0239 (7)	0.0303 (8)	0.0253 (7)	−0.0010 (6)	0.0029 (5)	0.0003 (6)
C23	0.0286 (7)	0.0274 (8)	0.0360 (8)	−0.0003 (6)	0.0004 (6)	−0.0020 (6)
C24	0.0248 (7)	0.0342 (8)	0.0326 (8)	0.0021 (6)	0.0000 (5)	−0.0100 (6)
C25	0.0320 (8)	0.0402 (9)	0.0233 (7)	−0.0004 (7)	0.0034 (5)	−0.0021 (6)
C26	0.0282 (7)	0.0292 (7)	0.0271 (7)	−0.0016 (6)	0.0016 (5)	0.0012 (6)
C100	0.0291 (7)	0.0233 (7)	0.0284 (7)	0.0019 (6)	−0.0019 (5)	0.0035 (6)
C101	0.0285 (7)	0.0244 (7)	0.0230 (6)	0.0033 (6)	−0.0025 (5)	0.0028 (5)
C102	0.0297 (7)	0.0209 (6)	0.0194 (6)	0.0045 (5)	−0.0009 (5)	−0.0011 (5)
C103	0.0286 (7)	0.0183 (6)	0.0196 (6)	0.0051 (5)	0.0024 (5)	−0.0012 (5)

O1—C100	1.3240 (19)	C12—H12A	0.9300
O1—H1O1	0.94 (3)	C13—H13A	0.9300
O2—C100	1.205 (2)	C14—C15	1.5135 (18)
O3—C103	1.2363 (18)	C14—H14A	0.9700
O4—C103	1.2837 (18)	C14—H14B	0.9700
N1—C17	1.4675 (17)	C15—H15A	0.9700
N1—C14	1.4688 (17)	C15—H15B	0.9700
N1—C7	1.4790 (17)	C16—C17	1.5194 (18)
N2—C16	1.4929 (17)	C16—H16A	0.9700
N2—C15	1.4976 (16)	C16—H16B	0.9700
N2—C18	1.5129 (17)	C17—H17A	0.9700
N2—H1N	0.943 (19)	C17—H17B	0.9700
C1—C6	1.389 (2)	C18—C19	1.497 (2)
C1—C2	1.395 (2)	C18—H18A	0.9700
C1—C7	1.5238 (19)	C18—H18B	0.9700
C2—C3	1.385 (2)	C19—C20	1.327 (2)
C2—H2A	0.9300	C19—H19A	0.9300
C3—C4	1.389 (3)	C20—C21	1.472 (2)
C3—H3A	0.9300	C20—H20A	0.9300
C4—C5	1.382 (3)	C21—C26	1.397 (2)
C4—H4A	0.9300	C21—C22	1.398 (2)
C5—C6	1.398 (2)	C22—C23	1.387 (2)
C5—H5A	0.9300	C22—H22A	0.9300
C6—H6A	0.9300	C23—C24	1.389 (2)
C7—C8	1.5267 (19)	C23—H23A	0.9300
C7—H7A	0.9800	C24—C25	1.385 (2)
C8—C13	1.393 (2)	C24—H24A	0.9300
C8—C9	1.394 (2)	C25—C26	1.390 (2)
C9—C10	1.389 (2)	C25—H25A	0.9300
C9—H9A	0.9300	C26—H26A	0.9300
C10—C11	1.380 (3)	C100—C101	1.487 (2)
C10—H10A	0.9300	C101—C102	1.323 (2)
C11—C12	1.391 (3)	C101—H10B	0.9300
C11—H11A	0.9300	C102—C103	1.5010 (19)
C12—C13	1.392 (2)	C102—H10C	0.9300
C100—O1—H1O1	110.6 (15)	N2—C15—H15A	109.7
C17—N1—C14	107.31 (10)	C14—C15—H15A	109.7
C17—N1—C7	112.44 (10)	N2—C15—H15B	109.7
C14—N1—C7	109.95 (11)	C14—C15—H15B	109.7
C16—N2—C15	110.08 (10)	H15A—C15—H15B	108.2
C16—N2—C18	109.73 (11)	N2—C16—C17	111.02 (11)
C15—N2—C18	112.20 (10)	N2—C16—H16A	109.4
C16—N2—H1N	106.2 (11)	C17—C16—H16A	109.4
C15—N2—H1N	108.8 (12)	N2—C16—H16B	109.4
C18—N2—H1N	109.7 (11)	C17—C16—H16B	109.4
C6—C1—C2	119.00 (14)	H16A—C16—H16B	108.0
C6—C1—C7	119.86 (13)	N1—C17—C16	109.63 (11)
C2—C1—C7	121.14 (13)	N1—C17—H17A	109.7
C3—C2—C1	120.71 (14)	C16—C17—H17A	109.7
C3—C2—H2A	119.6	N1—C17—H17B	109.7
C1—C2—H2A	119.6	C16—C17—H17B	109.7
C2—C3—C4	120.00 (16)	H17A—C17—H17B	108.2
C2—C3—H3A	120.0	C19—C18—N2	111.86 (11)
C4—C3—H3A	120.0	C19—C18—H18A	109.2
C5—C4—C3	119.90 (15)	N2—C18—H18A	109.2
C5—C4—H4A	120.1	C19—C18—H18B	109.2
C3—C4—H4A	120.1	N2—C18—H18B	109.2
C4—C5—C6	120.11 (15)	H18A—C18—H18B	107.9
C4—C5—H5A	119.9	C20—C19—C18	121.87 (13)
C6—C5—H5A	119.9	C20—C19—H19A	119.1
C1—C6—C5	120.28 (15)	C18—C19—H19A	119.1
C1—C6—H6A	119.9	C19—C20—C21	127.53 (14)
C5—C6—H6A	119.9	C19—C20—H20A	116.2
N1—C7—C1	111.23 (11)	C21—C20—H20A	116.2
N1—C7—C8	110.08 (11)	C26—C21—C22	118.15 (14)
C1—C7—C8	110.24 (11)	C26—C21—C20	119.13 (13)
N1—C7—H7A	108.4	C22—C21—C20	122.72 (13)
C1—C7—H7A	108.4	C23—C22—C21	120.93 (13)
C8—C7—H7A	108.4	C23—C22—H22A	119.5
C13—C8—C9	119.22 (14)	C21—C22—H22A	119.5
C13—C8—C7	121.79 (13)	C22—C23—C24	120.09 (15)
C9—C8—C7	118.95 (13)	C22—C23—H23A	120.0
C10—C9—C8	120.44 (16)	C24—C23—H23A	120.0
C10—C9—H9A	119.8	C25—C24—C23	119.81 (14)
C8—C9—H9A	119.8	C25—C24—H24A	120.1
C11—C10—C9	120.23 (16)	C23—C24—H24A	120.1
C11—C10—H10A	119.9	C24—C25—C26	119.97 (14)
C9—C10—H10A	119.9	C24—C25—H25A	120.0
C10—C11—C12	119.84 (15)	C26—C25—H25A	120.0
C10—C11—H11A	120.1	C25—C26—C21	121.03 (14)
C12—C11—H11A	120.1	C25—C26—H26A	119.5
C11—C12—C13	120.23 (16)	C21—C26—H26A	119.5
C11—C12—H12A	119.9	O2—C100—O1	123.66 (14)
C13—C12—H12A	119.9	O2—C100—C101	122.27 (14)
C12—C13—C8	120.03 (15)	O1—C100—C101	114.07 (13)
C12—C13—H13A	120.0	C102—C101—C100	123.96 (14)
C8—C13—H13A	120.0	C102—C101—H10B	118.0
N1—C14—C15	110.31 (11)	C100—C101—H10B	118.0
N1—C14—H14A	109.6	C101—C102—C103	123.90 (13)
C15—C14—H14A	109.6	C101—C102—H10C	118.0
N1—C14—H14B	109.6	C103—C102—H10C	118.0
C15—C14—H14B	109.6	O3—C103—O4	124.57 (13)
H14A—C14—H14B	108.1	O3—C103—C102	118.50 (13)
N2—C15—C14	110.00 (10)	O4—C103—C102	116.93 (12)
C6—C1—C2—C3	0.1 (2)	C7—N1—C14—C15	−173.18 (10)
C7—C1—C2—C3	−179.34 (13)	C16—N2—C15—C14	54.01 (14)
C1—C2—C3—C4	0.1 (2)	C18—N2—C15—C14	176.51 (11)
C2—C3—C4—C5	−0.4 (2)	N1—C14—C15—N2	−60.16 (14)
C3—C4—C5—C6	0.6 (2)	C15—N2—C16—C17	−54.01 (14)
C2—C1—C6—C5	0.1 (2)	C18—N2—C16—C17	−177.96 (10)
C7—C1—C6—C5	179.51 (13)	C14—N1—C17—C16	−63.17 (14)
C4—C5—C6—C1	−0.4 (2)	C7—N1—C17—C16	175.81 (11)
C17—N1—C7—C1	−50.90 (15)	N2—C16—C17—N1	59.32 (14)
C14—N1—C7—C1	−170.41 (11)	C16—N2—C18—C19	176.75 (11)
C17—N1—C7—C8	−173.39 (11)	C15—N2—C18—C19	54.05 (15)
C14—N1—C7—C8	67.10 (14)	N2—C18—C19—C20	−117.16 (14)
C6—C1—C7—N1	119.21 (14)	C18—C19—C20—C21	−179.45 (13)
C2—C1—C7—N1	−61.36 (17)	C19—C20—C21—C26	−177.76 (14)
C6—C1—C7—C8	−118.38 (14)	C19—C20—C21—C22	2.4 (2)
C2—C1—C7—C8	61.04 (17)	C26—C21—C22—C23	−1.1 (2)
N1—C7—C8—C13	36.25 (18)	C20—C21—C22—C23	178.80 (14)
C1—C7—C8—C13	−86.82 (16)	C21—C22—C23—C24	0.1 (2)
N1—C7—C8—C9	−145.97 (13)	C22—C23—C24—C25	0.7 (2)
C1—C7—C8—C9	90.96 (16)	C23—C24—C25—C26	−0.5 (2)
C13—C8—C9—C10	1.0 (2)	C24—C25—C26—C21	−0.5 (2)
C7—C8—C9—C10	−176.85 (14)	C22—C21—C26—C25	1.3 (2)
C8—C9—C10—C11	−0.1 (3)	C20—C21—C26—C25	−178.60 (13)
C9—C10—C11—C12	−0.6 (3)	O2—C100—C101—C102	173.65 (16)
C10—C11—C12—C13	0.4 (2)	O1—C100—C101—C102	−5.8 (2)
C11—C12—C13—C8	0.5 (2)	C100—C101—C102—C103	−177.35 (13)
C9—C8—C13—C12	−1.2 (2)	C101—C102—C103—O3	−175.41 (14)
C7—C8—C13—C12	176.58 (13)	C101—C102—C103—O4	4.2 (2)
C17—N1—C14—C15	64.23 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O4	0.943 (19)	1.740 (19)	2.6750 (15)	170.9 (17)
O1—H1O1···O4i	0.94 (3)	1.70 (3)	2.6270 (15)	168 (2)
C18—H18B···O3ii	0.97	2.56	3.3839 (18)	143
C15—H15A···O3ii	0.97	2.47	3.3463 (18)	151
C15—H15B···O2iii	0.97	2.46	3.1941 (19)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N⋯O4	0.943 (19)	1.740 (19)	2.6750 (15)	170.9 (17)
O1—H1O1⋯O4i	0.94 (3)	1.70 (3)	2.6270 (15)	168 (2)
C18—H18B⋯O3ii	0.97	2.56	3.3839 (18)	143
C15—H15A⋯O3ii	0.97	2.47	3.3463 (18)	151
C15—H15B⋯O2iii	0.97	2.46	3.1941 (19)	132

Symmetry codes: (i) ; (ii) ; (iii) .